The present invention relates to carboamidoalkyl norbornanes having the generic structure: ##STR3## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein R.sub.2 is methyl or hydrogen; R.sub.6 is methyl or hydrogen; R.sub.1, R.sub.3 or R.sub.7 represent methyl or hydrogen, with the proviso that one of R.sub.1, R.sub.3 and R.sub.7 represents methyl and the other two of R.sub.1, R.sub.3 and R.sub.7 represent hydrogen; wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or C.sub.1 -C.sub.3 lower alkyl, produced by the novel process of our invention and the novel compositions using one or more of such norbornane derivatives to alter, modify or enhance the aroma of certain consumable materials including perfumes, perfumed articles, colognes, foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos and smoking tobacco articles.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials some of which may be in short supply and to provide more uniform properties in the finished product.
Sweet, anise, grapefruit-like and green aroma and taste characteristics are desirable in several types of foodstuffs, chewing gums, medicinal products, toothpastes and chewing tobaccos.
Sweet and fruity aroma and taste nuances are desirable for augmenting or enhancing the aroma and taste of smoking tobaccos, smoking tobacco articles and smoking tobacco flavors.
Herbaceous, spearmint, spicy, caraway, basil, powdery, fruity, castoreum-like and anise aroma characteristics are desirable in several types of perfume compositions, perfumed articles and colognes.
Arctander, "Perfume and Flavor Chemicals", 1969, Volume I discloses the use in perfume compositions and in foodstuff flavors of camphene carbinyl acetate thus:
"1029: 2,2-Dimethyl-Delta-2-betanorbornane-2-ethylacetate "Camphene carbinyl acetate". ##STR4## Mild and sweet-woody odor with a floral-piney undertone. The commercial products are probably not well defined single chemicals, and great variations in odor have been observed. PA1 This ester has been developed in line with the research on Sandalwood type odors. The parent alcohol "Camphene carbinol" was once considered useful as a Sandalwood type material, but it has found more use as a sweetening and enriching ingredient in sophisticated Pine fragrances. The title ester finds limited use in perfume compositions of woody character, Fougeres, Pine fragrances, etc. and it blends very well with the Cyclohexanol derivatives, Ionones, iso-Bornylacetate, Nitromusks, etc"
Mellor and Webb, J. Chem. Soc. Perkin Trans II, 1974 (I) 26-31 discloses production of the compounds having the structures: ##STR5## together with several other methyl substituted isomers thereof in admixture, according to the reaction: ##STR6## The Mellor and Webb article, however, does not disclose the reaction to take place at low temperatures in the presence of an alkyl aluminum halide or dialkyl aluminum halide whereby but two isomers are produced in a controlled fashion in high yields. Furthermore, the Mellor and Webb article does not disclose the production of carboamido compounds but is merely limited to carboalkoxy compounds.
Thus, nothing in the prior art indicates production for organoleptic uses of compounds having the generic structure: ##STR7## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein R.sub.2 is methyl or hydrogen; R.sub.6 is methyl or hydrogen; R.sub.1, R.sub.3 or R.sub.7 represent methyl or hydrogen, with the proviso that one of R.sub.1, R.sub.3 and R.sub.7 represents methyl and the other two of R.sub.1, R.sub.3 and R.sub.7 represent hydrogen; wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or C.sub.1 -C.sub.3 lower alkyl.
Belgian Pat. No. 731,124 discloses the butyramide having the structure: ##STR8## for use in perfumery. It is indicated that this butyramide has a minty aroma and taste. The compound having the structure: ##STR9## is different in kind, both insofar as structure is concerned and insofar as organoleptic properties are concerned from the compounds of the instant invention.
Belgian Pat. No. 788,461 discloses the use in perfumery of N-phenyl-N-methyl-2-ethyl butyric acid amide which has the structure: ##STR10## It is indicated that this material has an herbaceous scent with a grapefruit-like note, being useful in perfumes, cosmetic products, foodstuffs and drinks. The structure of the compound of Belgian Pat. No. 788,461 is different in kind from the structure of the compounds of the instant case, and furthermore, the organoleptic properties of the compound of Belgian Patent 788,461 are different in kind from the organoleptic properties of the compounds of the instant case.
U.S. Pat. No. 4,193,936 issued on Mar. 18, 1980 (division of Ser. No. 796,973, filed on May 16, 1977, now U.S. Pat. No. 4,150,052) discloses substantially odorless non-volatile, physiologically active cooling compositions having the formula: ##STR11## wherein R is C.sub.1 -C.sub.9 alkyl, C.sub.3 -C.sub.7 cycloalkyl or a substituted phenyl radical of up to ten carbon atoms, containing as substituents one or more groups selected from C.sub.1 -C.sub.4 alkyl, hydroxy, C.sub.1 -C.sub.4 alkoxy, nitro and halogen. The compounds of U.S. Pat. No. 4,193,936 as well as those of U.S. Pat. No. 4,150,052, are different in kind from the compounds of our invention, and furthermore, their organoleptic properties are different in kind from the organoleptic properties of the compounds of our invention.